GREENWICH — Dan Dobryn’s watch beeps and he yells out the count.

“Eight minutes!” he calls. The 53-year-old former chemical engineer is the Hawkeye’s tactician, in charge, quite literally, of plotting her course to victory.

Around the 34-foot yacht, 19 sailboats in close proximity cut through Captain’s Harbor off the coast of Greenwich, all hoping to be the first across the start line when the gun goes off.

Heidi Matonis, stationed at the Hawkeye’s bow, calls out the position of the Silver Fox, just ahead.

“Got ’em, thanks Heidi!” replies Michael Burke — standing tall in the cockpit, blue eyes peering intently from the Hawkeye’s helm. She’s his vessel — and his passion.

He steers just feet behind Silver Fox. Ahead, the Bellerophon stands out from the weaving white boats with her size — 40 feet, the largest of any boat racing Wednesday — and her distinctive red color.

“They’re fast,” Colleen Cahill remarks, a hint of admiration in her voice as she mans the Hawkeye’s main sail.

“Ready about in five, four, three, two, one,” Burke counts down before tacking, a kind of turn that sends the sailboat through the eye of the wind.

An air horn indicates five minutes to the start.

Tactician and skipper execute a jibe and the boat changes direction, still navigating in the concentrated channel of boats.

With about two minutes left before the start, the Hawkeye follows Crazy Train toward the line.

“Let’s just not get too high,” Dobryn says. He worries about crossing the line too soon, which would disqualify them from the race. It’s a delicate balancing act — staying too far from the line is also bad; other boats will get ahead.

The perfect start requires being just below the line, moving at full speed and in clear air, when the air horn blows.

“Let’s trim for speed right now!” Dobryn calls to Cahill, the 33-year-old red head controlling the main sail. “Watch the tell-tales.”

Dobryn decides to edge toward the line with just over a minute left. But the boat approaches too quickly, so the crew executes a small turn to dump some speed.

The air horn blows one minute until the start. Voices jumble as the Hawkeye crew scrambles to trim the sails, dodge nearby boats and shout instructions to one another.

“Ease the jib for a second, we’ve got 30 seconds,” Dobryn shouts. “Ease the jib!”

“Ease, ease!” Burke chimes.

At 15 seconds, Dobryn’s oversized sailing watch begins beeping the passage of every second aloud. The crew is tensed.

“Alright let’s go for speed!” Dobryn yells. The Hawkeye heads for the line.

“Trim in that jib! Bring in the jib! Skirt, Heidi!” The bottom of the jib — a secondary sail in the front of the boat — is caught on a wire railing. Matonis dashes to free it so it can fill with air.

With a loud toot, the air horn goes off and the race has begun. The Hawkeye crosses the line and heads for the first mark.

“Come up a bit Michael!” Dobryn yells. “Heidi skirt!” The jib is caught again and she frees it once more.

Cahill, Matonis and Patrice Anibal, the fifth crew member, move to the side of the Hawkeye opposite the sail and sit with their legs dangling over the edge of the boat — ballasts. After all the action, the crew gets a moment of respite to look out over the evening light on Captain’s Harbor as the Hawkeye cruises on course.

“That was a good start,” says Cahill.

The Twilight Series

Ten years ago, the Old Greenwich and Indian Harbor yacht clubs started the Wednesday Night Twilight Series for sailboat racing. The weekly contest, which starts around 7 p.m. in the waters off Tod’s Point, allows skippers from the two clubs to compete.

“Scores are tabulated and competition is spirited,” said Michael Sullivan, membership director for the Old Greenwich club.

“The clubs definitely take pride in how the competitors do,” said Joel Labuzetta, waterfront director at Indian Harbor.

Unlike many local sailing races, such as the popular Ideal-18 contests, the Twilight Series allows boats of many designs to race against one another. The series is governed by Performance Handicap Racing Fleet rules. It separates boats into three divisions based on their model and size — both factors that might influence their speed.

Each sailboat is assigned a handicap — not unlike in golf — that allows it to compete fairly against boats of other designs.

“There’s some boats that you can be 20 minutes ahead of them, and you owe them so much time that you still lost,” said Cahill. “It all depends on what kind of boat you have and what boat you are racing against.”

The Hawkeye has a handicap of 150. If competing against a sailboat with a handicap of 159, it would owe that boat 9 seconds per mile, Burke explained.

On Wednesday, three boats raced in division one — the fastest, biggest boats — eight in the second division and nine in the third. Each week depending on which skippers show up, the numbers of boats in each division and in total may be different.

“By the end of the summer, I’ve almost figured out who’s in what division,” said Anibal, who is vice commodore of Old Greenwich Yacht Club. “But then the next year, I have to start all over again.”

First Mark

The Hawkeye rounds the first mark and heads for the second — a red buoy floating in the harbor — with its bow pointed directly at the sunset.

The evening light fingerpaints the waves in stripes of orange and pink. The wind has picked up since the Hawkeye left its mooring about 30 minutes earlier. Then only jumping bunkers, likely chased by bluefish or stripers below, broke the surface of the glassy water.

Behind the Hawkeye, Easy Red noses through the waves. The boat trails less than 10 feet off the Hawkeye’s stern, so close the Hawkeye sailors can hear the soft splash of its bow cutting through the water.

At the second mark, the crew pulls off a neat jibe to head back to the committee boat, which is serving as the third mark. Easy Red tails Hawkeye around the mark and passes her on the windward side, stealing the air from her sails for a moment and zapping her speed.

“Bring the traveler down, Colleen,” Dobryn says. “Ease the sheet a little bit.”

Cahill adjusts the main sail.

“OK, we’ve picked up to almost 6 knots,” Dobryn calls. “6.1 knots. We’re a little high … 6.6, 6.5.”

“Those are my brothers’ heights,” Burke jokes.

Hawkeye surfaces the waves, sail full on a beam reach. As it nears the third mark, Bellerophon, the speedy red sailboat, is cruising hard for the finish. A smaller white boat, Stampede, is struggling next to the red behemoth, which is blocking it from rounding the committee boat and continuing to race.

Hawkeye must round it too.

“Alright guys let’s get ready!” Dobryn calls. “So Colleen, I want you to center the traveler now.”

“5, 4, 3, 2 … up we go,” Burke says, throwing the wheel around.

Hawkeye heads back to the last mark, the sun nearly sinking behind the trees now.

Passion and perspective

For many in the Wednesday Night Twilight Series, sailing is an old flame, but for others it is a newfound love.

“Experienced and new members learning the sport are welcome to race on the club-owned Ideals or serve as crew on one of the PRHF boats,” said Michael Sullivan, membership director of OGYC.

Hawkeye’s Matonis, who grew up on the lakes of Minnesota, joined the racing crew two years ago, after making a New Year’s resolution to start sailing again. Cahill, a Port Chester special education teacher, started just four years ago, after a friend recommended she try it.

The most seasoned of the crew, Burke has been racing in Greenwich for 12 years, and sailing competitively — in races from Newport to Bermuda and around Long Island — since 1983.

“It’s been my passion for a long time,” he said.

Labuzetta, waterfront head at Indian Harbor, said his club has many boats that sail with multiple generations on them each week.

“The Wednesday races in particular are an opportunity to get out with families and have fun with it,” he said.

The pre-race bar scene and post-race pot luck add a healthy dose of socializing. The low $10 entry fee means the racing is accessible to many.

“I think people who might not race otherwise, get out on Wednesday,” said Labuzetta.

Getting on the water gives the sailors a dose of competition, as well as a new view of Greenwich.

“It feels so different to look at our town from the water as opposed to going out to the beach,” said Matonis. “It’s like a switched perspective and I feel like it’s almost like looking at a person upside down.”

To the finish

Hawkeye jibes around the last mark and heads for the finish line as the light fades from the pastel sky.

She sails “wing on wing” now, aiming to grab speed. Her main sail arcs out the port side; her jib, held out by a metal whisker pole, fans out to starboard.

“It looks like I’m relaxing but I’m keeping it square!” Matonis says. She stands, leaning her chest against the horizontal pole, arms crossed over it, like a kid leaning on an ice cream counter.

“That’s a lot of pressure,” Cahill laughs.

Hawkeye and her crew tail a few boats toward the finish line. Stampede, the small white Etchell, crosses the line just ahead. A toot of the air horn registers her finish, then Hawkeye’s.

“You got snookered there, Karen!” Burke calls to Stampede’s skipper Karen Varbaro, who has been racing in Greenwich longer than he has, about her encounter with the Bellerophon.

The race is over. Dobryn and Matonis take down the whisker pole. Hawkeye cruises easily, lazily to the mooring field near Old Greenwich Yacht Club.

The crew is pleased with the race. It’s been an off season for Hawkeye — her worst ever, Burke says — but in this race boat falls in the middle — fifth in its division of eight.

“Cigars and cookies!” Burke declares cheerfully and descends into Hawkeye’s cabin to retrieve them. When he returns to the cockpit, he holds out a rectangular box of pretzel rods. “Cigar?” he asks.

Dobryn gives a play-by-play review of Hawkeye’s performance and sips on seltzer, taking pictures of the last of the sunset.

When the boat is moored, the crew puts away sails, switches off electronics and prepares Hawkeye for a night’s rest. They motor back to the yacht club on a launch named Pride.; Twitter: @emiliemunson